Bill Simmons reads into Bill Belichick-Tom Brady split from leaked email amid Jordon Hudson controversy

Seven-time Super Bowl champ Tom Brady announced his free agency after 20 years at the New England Patriots in March 2020, stating that his goals did not align with coach Bill Belichick. He mentioned a natural tension between them that required separation.

Five years later, the Ringer’s Bill Simmons and Ryen Russillo discussed this tension, noting a hidden meaning behind Belichick's recent PR move: a statement after the CBS interview fiasco with his girlfriend, Jordon Hudson.

In the mail posted by Jordon on her Instagram, Bill gloated about how he turned the Patriots from being a franchise worth $500 million to $8 billion during his time with the team. This led the analysts to believe it provides much context about what happened with Tom Brady and Belichick in the mid-2010s.

“Everyone was like, ‘Patriot Way, Patriot Way, we’re just about Super Bowls,'” Simmons said. “But there was clearly some sort of ego thing and it’s two guys that really understood their place in history in a whole bunch of different ways, right?

Simmons continued: “I think that really explained to me why Brady didn’t end up [re-signing] with the Patriots because what everybody was writing about and doing the sports radio topic of ‘who’s more responsible for all the Super Bowls: Belichick or Brady?’ And the right answer was always both. They needed each other and that’s the answer."

Simmons further said that Tom Brady and Bill Belichick thought they were more responsible for the team's success.

What did Tom Brady say about his Patriots exit?

TB12 shared his two cents on free agency during one of his weekly newsletters in March 2025. The 47-year-old said he realized that a part of his job each offseason with FOX is keeping track of all the players who changed teams during free agency.

This realization led him to reflect on his journey with the concept when he got involved in free agency at the end of his career. Tom Brady revealed that a few days in March 2020 helped him realise that he had to decide his future with the franchise.

"The reality was, after twenty years together, a natural tension had developed between where Coach Belichick and I were headed in our careers, and where the Patriots were moving as a franchise. It was the kind of tension that could only be resolved by some kind of split or one of us reassessing our priorities." Brady wrote.

Belichick and Brady played 20 seasons together, including nine Super Bowl appearances and six rings.